CHEM2 Chemistry in Action Mark scheme

AQA Qualifications A-LEVEL CHEMISTRY CHEM2 Chemistry in Action Mark scheme 2420 June 2014 Version: 1.2 Final

Mark schemes are prepared by the Lead Assessment Writer and considered, together with the relevant questions, by a panel of subject teachers. This mark scheme includes any amendments made at the standardisation events which all associates participate in and is the scheme which was used by them in this examination. The standardisation process ensures that the mark scheme covers the students responses to questions and that every associate understands and applies it in the same correct way. As preparation for standardisation each associate analyses a number of students scripts: alternative answers not already covered by the mark scheme are discussed and legislated for. If, after the standardisation process, associates encounter unusual answers which have not been raised they are required to refer these to the Lead Assessment Writer. It must be stressed that a mark scheme is a working document, in many cases further developed and expanded on the basis of students reactions to a particular paper. Assumptions about future mark schemes on the basis of one year s document should be avoided; whilst the guiding principles of assessment remain constant, details will change, depending on the content of a particular examination paper. Further copies of this Mark Scheme are available from aqa.org.uk Copyright 2014 AQA and its licensors. All rights reserved. AQA retains the copyright on all its publications. However, registered schools/colleges for AQA are permitted to copy material from this booklet for their own internal use, with the following important exception: AQA cannot give permission to schools/colleges to photocopy any material that is acknowledged to a third party even for internal use within the centre.

Question Marking Guidance Mark Comments 1(a)(i) Award mark for X on the time axis at the point where the lines just become horizontal 1 Allow this mark If X is above the letters sh in the word show in Question 1(a)(ii) - in the range of lines 31 to 33 1(a)(ii) They are equal / the same Forward (rate) = Reverse / backward (rate) 1 Allow the word speed in this context. Ignore reference to concentration. 1(b) Both forward and reverse reactions occur at the same time both are occurring at once both occur all of the time both are ongoing both never stop 1 Ignore at equal rates. Ignore reference to concentration or equilibrium. The idea that both reactions occur simultaneously is essential. The simple idea of both reactions occurring is insufficient for the mark. 1(c)(i) M1 No effect / no change / none / stays the same 2 M2 requires correct M1 M2 Equal (number of) moles / molecules on both sides In M2, ignore reference to particles or atoms. 3 of 36

1(c)(ii) M1 Less time or it decreases or (equilibrium) reached faster (ie M1 is a reference to time taken) M2 More particles / molecules in a given volume / space the particles / molecules are closer together M3 More successful / productive collisions in a given time more collisions with E>E Act in a given time more frequent successful / productive collisions increased / greater successful / productive collision frequency / rate 3 If M1 is more time / it increases or no effect, then CE=0 for the clip. Reference to faster / increased rate / increased speed alone penalises M1, but mark on M2 and M3 If M1 is blank, then look for all three marks in the text. Ignore reference to reactants / products. Penalise M3 if an increase / decrease in the value of E Act is stated. 4 of 36

Question Marking Guidance Mark Comments 2(a) Amount / number / proportion / percentage / fraction / moles of molecules / particles 1 Penalise an incorrect qualification of the number eg NOT number of molecules with E greater than Ea Not atoms. 2(b) There are no molecules / particles with zero energy All of the molecules / particles are moving / have some energy 1 Not atoms. The answer should relate the energy to the molecules. 2(c) C (The most probable energy) 1 5 of 36

2(d) M1 The peak of the new curve is displaced to the right and lower than the original 2 M2 All of the following needed The new curve starts at the origin and should begin to separate from the original almost immediately and the new curve only crosses the original curve once and the total area under the new curve is approximately the same as the original and an attempt has been made to draw the new curve correctly towards the axis above the original curve but not to touch the original curve 2(e) None / no effect / stays the same 1 6 of 36

Question Marking Guidance Mark Comments 3(a)(i) 3Fe + Sb 2 S 3 3FeS + 2Sb 1 Or multiples. Ignore state symbols. 3(a)(ii) Fe Fe 2+ + 2e 1 Ignore charge on the electron unless incorrect. Or multiples. Credit the electrons being subtracted on the LHS. Ignore state symbols. 3(b)(i) Sb 2 S 3 + 4.5O 2 Sb 2 O 3 + 3SO 2 1 Or multiples. Ignore state symbols. 3(b)(ii) SO 3 or sulfur trioxide / sulfur (VI) oxide 1 Credit also the following ONLY H 2 SO 4 or sulfuric acid gypsum / CaSO 4 or plaster of Paris 7 of 36

3(c)(i) M1 (could be scored by a correct mathematical expression) M1 ΔH r = ΔH f (products) - ΔH f (reactants) 3 Correct answer gains full marks. Credit 1 mark for +104 (kj mol 1 ). a correct cycle of balanced equations / correct numbers of moles M2 = 2(+20) + 3( 394) ( 705) 3( 111) = 40 1182 + 705 + 333 = 1142 ( 1038) (This also scores M1) M3 = 104 (kj mol 1 ) For other incorrect or incomplete answers, proceed as follows: check for an arithmetic error (AE), which is either a transposition error or an incorrect multiplication; this would score 2 marks. If no AE, check for a correct method; this requires either a correct cycle with 3CO, 2Sb and 3CO 2 a clear statement of M1 which could be in words and scores only M1. (Award 1 mark ONLY for + 104) 3(c)(ii) It / Sb is not in its standard state Standard state (for Sb) is solid / (s) (Sb) liquid is not its standard state 1 Credit a correct definition of standard state as an alternative to the words standard state. QoL 3(c)(iii) Reduction reduced redox 1 8 of 36

3(d) Low-grade ore extraction / it uses (cheap) scrap / waste iron / steel is a single-step process uses / requires less / low(er) energy 1 Ignore references to temperature / heat or labour or technology. 9 of 36

Question Marking Guidance Mark Comments 4(a) M1 Used in a barium meal / barium swallow / barium enema (used to absorb) X-rays 2 Credit a correct reference to M1 written in the explanation in M2 unless contradictory. M2 BaSO 4 / barium sulfate / it is insoluble For M2 penalise obvious reference to barium or to barium ions being insoluble. 4(b) Mg(OH) 2 + 2HCl MgCl 2 + 2H 2 O 1 Or multiples. Ignore state symbols. 4(c) It / magnesium hydroxide is insoluble / insufficiently soluble / sparingly soluble / less soluble than barium hydroxide / forms low concentration solutions 1 Weak alkali alone is insufficient. Formation of a precipitate needs explanation. 4(d) TiCl 4 + 2Mg 2MgCl 2 + Ti 1 Or multiples. Ignore state symbols. 10 of 36

4(e) M1 Hydrogen / H 2 produced an equation to produce hydrogen / H 2 ( eg Mg + 2H 2 O Mg(OH) 2 + H 2 ) ( eg Mg + H 2 O MgO + H 2 ) M2 requires correct M1 risk of explosion forms explosive mixture (with air) (highly) flammable 2 For M1 Do not penalise an incorrect equation; the mark is for H 2 or hydrogen. Award one mark only for exothermic reaction with steam / H 2 O for a student who has not scored M1 Ignore violent reaction. 11 of 36

Question Marking Guidance Mark Comments 5(a)(i) M1 Initiation Cl 2 2Cl 4 Penalise absence of dot once only. M2 First propagation Cl + CHF 3 CF 3 + HCl Penalise + or charges every time M3 Second propagation Cl 2 + CF 3 CClF 3 + Cl Credit CF 3 with the radical dot above / below / to either side. M4 Termination (must make C 2 F 6 ) 2 CF 3 C 2 F 6 or CF 3 CF 3 Mark independently. 5(a)(ii) ultra-violet / uv / sun light (very) high temperature 500 o C T 1000 o C 773 K T 1273 K 1 12 of 36

5(b)(i) Cl chlorine atom / chlorine (free-) radical / Cl (atom) 1 Not chlorine alone. Credit Cl alone on this occasion. 5(b)(ii) 2O 3 3O 2 1 Or multiples. Ignore state symbols. If the correct answer is on the line clearly identified below some working, then ignore any working. 13 of 36

Question Marking Guidance Mark Comments 6(a)(i) M1 (+) 4 IV 2 M2 (+) 6 VI 6(a)(ii) It / Chlorine has gained / accepted electron(s) Correctly balanced half-equation eg Cl 2 + 2e 2Cl 1 Credit 1 or 2 electrons but not lone pair. The idea of reduction alone is not enough. 6(b)(i) 6KI + 7H 2 SO 4 6KHSO 4 + 3I 2 + S + 4H 2 O 1 6(b)(ii) 2I I 2 + 2e 8I 4I 2 + 8e 6(b)(iii) H 2 SO 4 + 8H + + 8e H 2 S + 4H 2 O SO 4 2 + 10H + + 8e H 2 S + 4H 2 O 1 Ignore charge on the electron unless incorrect. Or multiples. Credit the electrons being subtracted on the LHS. Ignore state symbols. 1 Ignore charge on the electron unless incorrect. Or multiples. Credit the electrons being subtracted on the RHS. Ignore state symbols. 14 of 36

6(c)(i) Ag + + I AgI ONLY 1 Ignore state symbols. Not multiples. 6(c)(ii) The precipitate / solid / it does not dissolve / is insoluble / remains a white / cream / yellow solid / precipitate stays the same no (visible / observable) change no effect / no reaction 1 Ignore nothing (happens). Ignore no observation. 6(c)(iii) The silver nitrate is acidified to react with / remove (an)ions that would interfere with the test prevent the formation of other silver precipitates / insoluble silver compounds that would interfere with the test remove (other) ions that react with the silver nitrate react with / remove carbonate / hydroxide / sulfite (ions) 1 Credit a correct reference to ions that give a false positive. Do not penalise an incorrect formula for an ion that is written in addition to the name. If only the formula of the ion is given, it must be correct. Ignore sulfate. 6(c)(iv) HCl would form a (white) precipitate / (white) solid (with silver nitrate and this would interfere with the test) 1 It is not sufficient simply to state either that it will interfere or simply that the ions / compounds react to form AgCl 15 of 36

6(d)(i) Any one from to sterilise / disinfect water to destroy / kill microorganisms / bacteria / microbes / pathogens 1 Ignore to clean water. Ignore water purification and germs. Credit remove bacteria etc / prevent algae. 6(d)(ii) The (health) benefit outweighs the risk a clear statement that once it has done its job, little of it remains used in (very) dilute concentrations / small amounts / low doses 1 6(d)(iii) Cl 2 + H 2 O HClO + HCl Cl 2 + H 2 O 2H + + ClO + Cl 2Cl 2 + 2H 2 O 4HCl + O 2 1 Credit HOCl or ClOH Or multiples. Credit other ionic or mixed representations. Ignore state symbols. 6(e) In either order - Both required for one mark only NaClO ( NaOCl) and NaCl 1 Credit correct ionic formulae. Give credit for answers in equations unless contradicted. 16 of 36

Question Marking Guidance Mark Comments 7(a)(i) M1 (Compounds / molecules with) the same structural formula M2 with atoms / bonds / groups arranged differently in space atoms / bonds / groups with different spatial arrangements / different orientation 2 Penalise M1 if same structure or different structural / displayed formula. Ignore references to same molecular formula or same empirical formula. Mark independently. 7(a)(ii) 1 Credit C H 3 C Credit C 2 H 5 Penalise C CH 3 CH 2 17 of 36

7(b) M1 Br 2 bromine (water) bromine (in CCl 4 / organic solvent) M2 Isomer 1: decolourised / goes colourless / loses its colour M3 Isomer 2: remains orange / red / yellow / brown / the same no reaction / no (observable) change reference to colour going to the cyclopentane layer Alternatives : potassium manganate(vii) M1 KMnO 4 in acid M2 colourless M3 purple M1 KMnO 4 in alkali / neutral M2 brown solid M3 purple 3 If M1, has no reagent or an incorrect reagent, CE=0 Ignore acidified. For M1 penalise Br (or incorrect formula of other correct reagent), but mark on. For M1, it must be a whole reagent and/or correct formula. If oxidation state given in name, it must be correct. If manganate manganate(iv) or incorrect formula, penalise M1, but mark on. Credit for the use of iodine M1 iodine (solution / in KI) M2 colourless M3 (brown) to purple (credit no change) Ignore goes clear. Ignore nothing (happens). Ignore no observation. Credit for the use of concentrated H 2 SO 4 M1 concentrated H 2 SO 4 M2 brown M3 no change / colourless No credit for combustion observations. 18 of 36

7(c)(i) (Both infrared spectra show an absorption in range) 1620 to 1680 (cm 1 ) 1 Ignore reference to other ranges (eg for C H or C C). 7(c)(ii) The fingerprint (region) / below 1500 cm 1 will be different or its fingerprinting will be different different absorptions / peaks are seen (in the region) below 1500 cm 1 (or a specified region within the fingerprint range) 1 Allow the words dip spike low transmittance as alternatives for absorption. QoL 7(d) 1 All bonds must be drawn. Ignore bond angles. 19 of 36

7(e)(i) M1 Electrophilic addition 5 M1 both words needed. M2 must show an arrow from the double bond towards the H atom of the H Br molecule M3 must show the breaking of the H Br bond M4 is for the structure of the tertiary carbocation M5 must show an arrow from the lone pair of electrons on the negatively charged bromide ion towards the positively charged carbon atom of either a secondary or a tertiary carbocation Penalise one mark from their total if half-headed arrows are used. M2 Ignore partial negative charge on the double bond. M3 Penalise incorrect partial charges on H Br bond and penalise formal charges. Penalise M4 if there is a bond drawn to the positive charge. Penalise once only in any part of the mechanism for a line and two dots to show a bond. Max 3 of any 4 marks in the mechanism for wrong organic reactant or wrong organic product (if shown) or secondary carbocation. Max 2 of any 4 marks in the mechanism for use of bromine. Do not penalise the correct use of 'sticks. For M5, credit attack on a partially positively charged carbocation structure but penalise M4 NB The arrows here are double-headed 20 of 36

7(e)(ii) M1 Reaction goes via intermediate carbocations / carbonium ions M2 (scores both marks and depends on M1) Tertiary carbocation / carbonium ion is more stable (than the secondary carbocation / carbonium ion) Secondary carbocation / carbonium ion is less stable (than the tertiary carbocation / carbonium ion) 2 M1 is a lower demand mark for knowledge that carbocations are involved. M2 is of higher demand and requires the idea that the secondary carbocation is less stable or the tertiary carbocation is more stable. Reference to incorrect chemistry is penalised. A carbocation may be defined in terms of alkyl groups / number of carbon atoms, rather than formally stated. 21 of 36

7(f) M1 Elimination 5 M1 credit base elimination but no other qualifying prefix. M2 must show an arrow from the lone pair on oxygen of a negatively charged hydroxide ion to a correct H atom M3 must show an arrow from a correct C H bond adjacent to the C Br bond to a correct C C bond. Only award if an arrow is shown attacking the H atom of a correct adjacent C H bond (in M2) M4 is independent provided it is from their original molecule BUT penalise M2, M3 and M4 if nucleophilic substitution shown Award full marks for an E1 mechanism in which M2 is on the correct carbocation NB The arrows here are double-headed Penalise one mark from their total if half-headed arrows are used. Penalise M2 if covalent KOH Penalise M4 for formal charge on C or Br of the C Br bond or incorrect partial charges on C Br Penalise M4 if an additional arrow is drawn from the Br of the C Br bond to, for example, K + Ignore other partial charges. Penalise once only in any part of the mechanism for a line and two dots to show a bond. Max 2 of any 3 marks in the mechanism for wrong reactant or wrong organic product (if shown) or a correct mechanism that leads to the alkene 2-methylbut-2-ene Credit the correct use of sticks for the molecule except for the C H being attacked. M5 hydroxide ion behaves as a base / proton acceptor / electron pair donor / lone pair donor Penalise M5 if nucleophile. 22 of 36

Question Marking Guidance Mark Comments 8(a)(i) M1 double-headed curly arrow from the lone pair of the bromide ion to the C atom of the CH 2 2 Penalise additional arrows. M2 double-headed arrow from the bond to the O atom As follows 8(a)(ii) M1 nucleophilic substitution 2 M1 both words needed (allow phonetic spelling). M2 1-bromo(-2-)methylpropane M2 Require correct spelling in the name but ignore any hyphens or commas. 23 of 36

8(b) M1 hydrolysis 3 For M1 give credit for hydration on this occasion only. M2 C N with absorption range 2220 2260 (cm 1 ) M3 O H(acids) with absorption range 2500 3000 (cm 1 ) C=O with absorption range 1680 1750 (cm 1 ) C O with absorption range 1000 1300 (cm 1 ) Credit 1 mark from M2 and M3 for identifying C N and either O H(acids) or C=O or C O without reference to wavenumbers or with incorrect wavenumbers. Apply the list principle to M3 8(c)(i) M1 Yield / product ester increases / goes up / gets more M2 (By Le Chatelier s principle) the position of equilibrium is driven / shifts / moves to the right / L to R / in the forward direction / to the product(s) 3 If no reference to M1, marks M2 and M3 can still score BUT if M1 is incorrect CE=0 M3 requires a correct statement in M2 (The position of equilibrium moves) to oppose the increased concentration of ethanol to oppose the increased moles of ethanol to lower the concentration of ethanol to oppose the change and decrease the ethanol If there is reference to pressure award M1 ONLY. 24 of 36

8(c)(ii) M1 Catalysts provide an alternative route / pathway / mechanism surface adsorption / surface reaction occurs 2 For M1, not simply provides a surface as the only statement. M1 may be scored by reference to a specific example. M2 that has a lower / reduced activation energy lowers / reduces the activation energy Penalise M2 for reference to an increase in the energy of the molecules. For M2, the student may use a definition of activation energy without referring to the term. Reference to an increase in successful collisions in unit time alone is not sufficient for M2 since it does not explain why this has occurred. 25 of 36

Question Marking Guidance Mark Comments 9(a) M1 C 6 H 12 O 6 2CH 3 CH 2 OH + 2CO 2 (2C 2 H 5 OH) M2 and M3 Any two conditions in any order for M2 and M3 from (enzymes from) yeast or zymase 25 C T 42 C 298 K T 315 K anaerobic / no oxygen / no air neutral ph M4 (fractional) distillation or GLC 5 Penalise C 2 H 6 O for ethanol in M1 Mark M2 and M3 independently. A lack of oxygen can mean either without oxygen or not having enough oxygen and does not ensure no oxygen, therefore only credit lack of oxygen if it is qualified. Penalise bacteria, phosphoric acid, high pressure using the list principle. Ignore reference to aqueous or water (ie not part of the list principle). M5 Carbon-neutral in this context means There is no net / overall (annual) carbon dioxide / CO 2 emission to the atmosphere For M5 must be about CO 2 and the atmosphere. The idea that the carbon dioxide / CO 2 given out equals the carbon dioxide / CO 2 that was taken in from the atmosphere. There is no change in the total amount / level of carbon dioxide / CO 2 present in the atmosphere 26 of 36

9(b) M1 q = m c ΔT (this mark for correct mathematical formula) 5 Full marks for M1, M2 and M3 for the correct answer. M2 = (75 4.18 5.5) 1724 (J) 1.724 (kj) 1.72 (kj) 1.7 (kj) (also scores M1) In M1, do not penalise incorrect cases in the formula. Ignore incorrect units in M2 M3 Using 0.0024 mol therefore ΔH = 718 (kj mol 1 ) (Accept a range from 708 to 719 but do not penalise more than 3 significant figures) M4 and M5 in any order Any two from incomplete combustion heat loss heat capacity of Cu not included some ethanol lost by evaporation not all of the (2.40 10 3 mol) ethanol is burned / reaction is incomplete Penalise M3 ONLY if correct numerical answer but sign is incorrect. Therefore +718 gains two marks. If units are quoted in M3 they must be correct If ΔT = 278.5, CE for the calculation and penalise M2 and M3 If c = 4.81 (leads to 1984) penalise M2 ONLY and mark on for M3 = 827 27 of 36

9(c)(i) M1 enthalpy / heat / energy change (at constant pressure) or enthalpy / heat / energy needed in breaking / dissociating (a) covalent bond(s) M2 averaged for that type of bond over different / a range of molecules / compounds 2 Ignore bond making. Ignore reference to moles. 28 of 36

9(c)(ii) M1 B(reactants) B(products) = ΔH Sum of bonds broken Sum of bonds formed = ΔH B(C-C) + B(C-O) + B(O-H) + 5B(C-H) + 3B(O=O) 4B(C=O) 6B(O H) = ΔH = 1279 M2 (also scores M1) 348+360+463+5(412)+ 3B(O=O) (3231) (or 2768 if O H cancelled) 4(805) 6(463) = ΔH = 1279 (5998) (or 5535 if O H cancelled) 3B(O=O) = 1488 (kj mol 1 ) M3 B(O=O) = 496 (kj mol 1 ) 3 Correct answer gains full marks. Credit 1 mark for 496 (kj mol 1 ) For other incorrect or incomplete answers, proceed as follows check for an arithmetic error (AE), which is either a transposition error or an incorrect multiplication; this would score 2 marks (M1 and M2). If no AE, check for a correct method; this requires either a correct cycle with 2CO 2 and 3H 2 O a clear statement of M1 which could be in words and scores only M1. Credit a maximum of one mark if the only scoring point is bonds formed adds up to 5998 (or 5535) bonds broken includes the calculated value of 3231 (or 2768). Award 1 mark for 496 Students may use a cycle and gain full marks 29 of 36

General principles applied to marking CHEM2 papers by CMI+ (June 2014) It is important to note that the guidance given here is generic and specific variations may be made at individual standardising meetings in the context of particular questions and papers. Basic principles Examiners should note that throughout the mark scheme, items that are underlined are required information to gain credit. Occasionally an answer involves incorrect chemistry and the mark scheme records CE = 0, which means a chemical error has occurred and no credit is given for that section of the clip or for the whole clip. 1. The List principle and the use of ignore in the mark scheme If a question requires one answer and a student gives two answers, no mark is scored if one answer is correct and one answer is incorrect. There is no penalty if both answers are correct. NB Certain answers are designated in the mark scheme as those which the examiner should Ignore. These answers are not counted as part of the list and should be ignored and will not be penalised. 2. Incorrect case for element symbol The use of an incorrect case for the symbol of an element should be penalised once only within a clip. For example, penalise the use of h for hydrogen, CL for chlorine or br for bromine. 30 of 36

3. Spelling In general The names of chemical compounds and functional groups must be spelled correctly to gain credit. Phonetic spelling may be acceptable for some chemical terminology. NB Some terms may be required to be spelled correctly or an idea needs to be articulated with clarity, as part of the Quality of Language (QoL) marking. These will be identified in the mark scheme and marks are awarded only if the QoL criterion is satisfied. 4. Equations In general Equations must be balanced. When an equation is worth two marks, one of the marks in the mark scheme will be allocated to one or more of the reactants or products. This is independent of the equation balancing. State symbols are generally ignored, unless specifically required in the mark scheme. 31 of 36

5. Reagents The command word Identify, allows the student to choose to use either the name or the formula of a reagent in their answer. In some circumstances, the list principle may apply when both the name and the formula are used. Specific details will be given in mark schemes. The guiding principle is that a reagent is a chemical which can be taken out of a bottle or container. Failure to identify complete reagents will be penalised, but follow-on marks (e.g. for a subsequent equation or observation) can be scored from an incorrect attempt (possibly an incomplete reagent) at the correct reagent. Specific details will be given in mark schemes. For example, no credit would be given for the cyanide ion or CN when the reagent should be potassium cyanide or KCN; the hydroxide ion or OH when the reagent should be sodium hydroxide or NaOH; the Ag(NH 3 ) 2 + ion when the reagent should be Tollens reagent (or ammoniacal silver nitrate). In this example, no credit is given for the ion, but credit could be given for a correct observation following on from the use of the ion. Specific details will be given in mark schemes. In the event that a student provides, for example, both KCN and cyanide ion, it would be usual to ignore the reference to the cyanide ion (because this is not contradictory) and credit the KCN. Specific details will be given in mark schemes. 6. Oxidation states In general, the sign for an oxidation state will be assumed to be positive unless specifically shown to be negative. 7. Marking calculations In general A correct answer alone will score full marks unless the necessity to show working is specifically required in the question. An arithmetic or transposition error will result in a one mark penalty if further working is correct. A chemical error will usually result in at least a two mark penalty; often no marks are awarded. 32 of 36

8. Organic reaction mechanisms Curly arrows should originate either from a lone pair of electrons or from a bond. The following representations should not gain credit and will be penalised each time within a clip... H 3. H 3 C Br H 3 C Br C _ : OH.. _ OH For example, the following would score zero marks H Br H 3 C HO C H Br When the curly arrow is showing the formation of a bond to an atom, the arrow can go directly to the relevant atom, alongside the relevant atom or more than half-way towards the relevant atom. The following are acceptable representations of ions, both in equations and in mechanisms: :OH or :OH :CN or :CN NO 2 or NO 2 In free-radical substitution The absence of a radical dot should be penalised once only within a clip. The use of double-headed arrows or the incorrect use of half-headed arrows in free-radical mechanisms should be penalised once only within a clip In mass spectrometry fragmentation equations, the absence of a radical dot on the molecular ion and on the free-radical fragment would be considered to be two independent errors and both would be penalised if they occurred within the same clip. 33 of 36

9. Organic structures In general Displayed formulae must show all of the bonds and all of the atoms in the molecule, but need not show correct bond angles. Bonds should be drawn correctly between the relevant atoms. This principle applies in all cases where the attached functional group contains a carbon atom, e.g nitrile, carboxylic acid, aldehyde and acid chloride. The carbon-carbon bond should be clearly shown. Wrongly bonded atoms will be penalised on every occasion. (see the examples below) The same principle should also be applied to the structure of alcohols. For example, if students show the alcohol functional group as C HO, they should be penalised on every occasion. Latitude should be given to the representation of C C bonds in alkyl groups, given that CH 3 is considered to be interchangeable with H 3 C even though the latter would be preferred. Similar latitude should be given to the representation of amines where NH 2 C will be allowed, although H 2 N C would be preferred. Poor presentation of vertical C CH 3 bonds or vertical C NH 2 bonds should not be penalised. For other functional groups, such as OH and CN, the limit of tolerance is the half-way position between the vertical bond and the relevant atoms in the attached group. By way of illustration, the following would apply. CH 3 C C C OH C C CH 3 CH 3 CH 2 OH allowed allowed not allowed not allowed not allowed NH 2 NO 2 NH 2 C C NH 2 allowed allowed allowed allowed not allowed NH 2 34 of 36

CN C C COOH C C C CN COOH COOH not allowed not allowed not allowed not allowed not allowed CHO C C C COCl C C C CHO CHO COCl COCl not allowed not allowed not allowed not allowed not allowed not allowed In most cases, the use of sticks to represent C H bonds in a structure should not be penalised. The exceptions will include structures in mechanisms when the C H bond is essential (e.g. elimination reactions in haloalkanes) and when a displayed formula is required. Some examples are given here of structures for specific compounds that should not gain credit CH 3 COH for ethanal CH 3 CH 2 HO for ethanol OHCH 2 CH 3 for ethanol C 2 H 6 O for ethanol CH 2 CH 2 for ethene CH 2.CH 2 for ethene CH 2 :CH 2 for ethane NB Exceptions may be made in the context of balancing equations 35 of 36

Each of the following should gain credit as alternatives to correct representations of the structures. 10. Organic names CH 2 = CH 2 for ethene, H 2 C=CH 2 CH 3 CHOHCH 3 for propan-2-ol, CH 3 CH(OH)CH 3 As a general principle, non-iupac names or incorrect spelling or incomplete names should not gain credit. Some illustrations are given here. but-2-ol 2-hydroxybutane butane-2-ol 2-butanol ethan-1,2-diol 2-methpropan-2-ol 2-methylbutan-3-ol 3-methylpentan 3-mythylpentane 3-methypentane propanitrile aminethane 2-methyl-3-bromobutane 3-bromo-2-methylbutane 3-methyl-2-bromobutane 2-methylbut-3-ene difluorodichloromethane should be butan-2-ol should be butan-2-ol should be butan-2-ol should be butan-2-ol should be ethane-1,2-diol should be 2-methylpropan-2-ol should be 3-methylbutan-2-ol should be 3-methylpentane should be 3-methylpentane should be 3-methylpentane should be propanenitrile should be ethylamine (although aminoethane can gain credit) should be 2-bromo-3-methylbutane should be 2-bromo-3-methylbutane should be 2-bromo-3-methylbutane should be 3-methylbut-1-ene should be dichlorodifluoromethane 36 of 36